Final answer:
The dimerization ability of radicals typically increases with their stability, following the trend: tertiary > secondary > primary. For aromatic compounds, substituent effects in different positions (ortho, meta, para) influence stability and dimerization behavior. A recommended reading is 'Advanced Organic Chemistry' by Carey and Sundberg.
Step-by-step explanation:
The question you are asking relates to the dimerization abilities of different radicals in organic chemistry. The dimerization ability often increases with the stability of the radical, which means the more substituted the radical center is, the greater its tendency to dimerize due to lower reactivity and a higher degree of stabilization through hyperconjugation and other effects. In general, the order of radical stability, and thereby dimerization tendency, usually follows this trend: tertiary (R3C·) > secondary (R2CH·) > primary (RCH2·). The Triphenylmethyl radical is an example of a stable radical due to its extensive resonance stabilization, leading to a higher ability to dimerize via the Gomberg dimerization process.
To understand the specific dimerization behavior of aromatic compounds, such as those described in your question, it is important to consider the electronic and steric effects imposed by the substituents attached to the aromatic ring. For instance, substituents in the ortho, meta, and para positions have different steric and electronic influences that can affect the stability of the radical and its dimerization ability.
A valid source to read more about these concepts in organic chemistry, including dimerization reactions, radical stability, and the effects of substituents on aromatic compounds, would be Advanced Organic Chemistry by Francis A. Carey and Richard J. Sundberg. This textbook provides a comprehensive overview of the principles and reactions pertinent to organic chemistry and is commonly used in advanced undergraduate and graduate courses.